Wow. I know who Cuban is but I didn't know he was a Randoid. (self mocking like "dito-head")
Atlas Shrugged is the only way to go if you can only read one. But if your pal likes (shorter) non-fiction I'd suggest Philosophy: Who Needs it? as the only way to go. (again, if you read just one... but ya can't. She's like potato chips, or, if your Dan Quayle, potatoe chips)
Fountainhead was what Cuban discussed, and that's what I talked with to my partner about. I told him he could do what I did, you can skip like whole paragraphs. Rand is interesting, but rambles and is redundant at a point. She's not the best writer. LOL.
Honestly, it was intersting. I didn't know much about Cuban other than broadcast.com and that he owns the Mavs, but he's quite an intersting fellow.